Substrate-Controlled Cu(OAc)(2)-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source

[Image: see text] A substrate-controlled stereoselective semi-reduction of alkynes with MeOH as the hydrogen source has been developed, and readily available Cu(OAc)(2) (copper acetate) is utilized as an optimal catalyst. The detailed investigation of the mechanism revealed distinct catalytic proces...

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Autores principales: Huang, Jiuzhong, Li, Xiaoning, Wen, Huiling, Ouyang, Lu, Luo, Nianhua, Liao, Jianhua, Luo, Renshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8154033/
https://www.ncbi.nlm.nih.gov/pubmed/34056327
http://dx.doi.org/10.1021/acsomega.1c01083
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author Huang, Jiuzhong
Li, Xiaoning
Wen, Huiling
Ouyang, Lu
Luo, Nianhua
Liao, Jianhua
Luo, Renshi
author_facet Huang, Jiuzhong
Li, Xiaoning
Wen, Huiling
Ouyang, Lu
Luo, Nianhua
Liao, Jianhua
Luo, Renshi
author_sort Huang, Jiuzhong
collection PubMed
description [Image: see text] A substrate-controlled stereoselective semi-reduction of alkynes with MeOH as the hydrogen source has been developed, and readily available Cu(OAc)(2) (copper acetate) is utilized as an optimal catalyst. The detailed investigation of the mechanism revealed distinct catalytic processes for the (Z)- and (E)-alkenes, respectively. As a result, a diversity of alkynes (including terminal, internal alkynes etc.) were compatible under the mild reaction conditions. Furthermore, the high proportion of deuterium in Z-alkenes (up to 96%) was obtained using d(4)-methanol as a solvent.
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spelling pubmed-81540332021-05-27 Substrate-Controlled Cu(OAc)(2)-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source Huang, Jiuzhong Li, Xiaoning Wen, Huiling Ouyang, Lu Luo, Nianhua Liao, Jianhua Luo, Renshi ACS Omega [Image: see text] A substrate-controlled stereoselective semi-reduction of alkynes with MeOH as the hydrogen source has been developed, and readily available Cu(OAc)(2) (copper acetate) is utilized as an optimal catalyst. The detailed investigation of the mechanism revealed distinct catalytic processes for the (Z)- and (E)-alkenes, respectively. As a result, a diversity of alkynes (including terminal, internal alkynes etc.) were compatible under the mild reaction conditions. Furthermore, the high proportion of deuterium in Z-alkenes (up to 96%) was obtained using d(4)-methanol as a solvent. American Chemical Society 2021-04-22 /pmc/articles/PMC8154033/ /pubmed/34056327 http://dx.doi.org/10.1021/acsomega.1c01083 Text en © 2021 The Authors. Published by American Chemical Society Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Huang, Jiuzhong
Li, Xiaoning
Wen, Huiling
Ouyang, Lu
Luo, Nianhua
Liao, Jianhua
Luo, Renshi
Substrate-Controlled Cu(OAc)(2)-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source
title Substrate-Controlled Cu(OAc)(2)-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source
title_full Substrate-Controlled Cu(OAc)(2)-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source
title_fullStr Substrate-Controlled Cu(OAc)(2)-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source
title_full_unstemmed Substrate-Controlled Cu(OAc)(2)-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source
title_short Substrate-Controlled Cu(OAc)(2)-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source
title_sort substrate-controlled cu(oac)(2)-catalyzed stereoselective semi-reduction of alkynes with meoh as the hydrogen source
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8154033/
https://www.ncbi.nlm.nih.gov/pubmed/34056327
http://dx.doi.org/10.1021/acsomega.1c01083
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